New York's Scariest Neighborhood: The Upper East Side

By Cait Etherington | From Get To Know Friday, October 25, 2019

Photo by Carter Horsley, of a spirited building at the Northeast corner of York Avenue and 86th Street

Many New Yorkers fear the Upper East Side and for many reasons. But once a year, there is more to run away from than strict schoolmasters, dreaded relatives, dentists, and shrinks. At Halloween, the Upper East Side’s truly scary side comes out of hiding. For many years now, the neighborhood has been celebrated as one of the city’s top destinations for tricks, treats, and elaborate Halloween home makeovers. As our investigation discovered, the title is well deserved. The neighborhood is one of the city’s most popular trick-or-treating destinations and home to some of the best-haunted houses in the city, including the Mayor’s own Gracie Mansion.

East 81st Street

78th Street—A Trick-or-Treating Hotspot

One of the city’s top places to be on Halloween night is East 78th Street between Lexington and Park Avenue. This particular stretch of 78th Street has long been considered a top spot for trick-or-treating on the Upper East Side and one of the most popular trick-or-treating locations in all five boroughs. In the past, nearly all residents on the block have participated in the spectacle and collectively given away thousands of units of candy. Unfortunately, since 2017, multiple homes on the street have been under construction, putting a minor damper on the street’s Halloween festivities. Still, despite the construction, East 78th remains a major hub of Halloween activity.

Barded up building along East 78th Street

Haunted Houses

The Upper East Side has its share of abandoned mansions (including a long-abandoned multi-level flat at 907 E. 5th Street belonging to heiress Huguette Clark) and buildings with frightening histories (Saddam Hussein allegedly had a torture chamber in the basement at 14 East 79th Street). Without the help of a clairvoyant, it is impossible to know whether either of these addresses is truly haunted. What is clear is that in the Upper East Side, many wealthy residents love to carry out elaborate home decorating projects at this time of year. While decorations tend to be predictable and veer to the expected bats, skeletons, caution tape, and pumpkins, some local residents take their Halloween decorating more seriously than others.

In recent years, a stretch of houses on the south side of 81st Street west of Madison Avenue has put on a particularly good Halloween show. Madonna’s block, which stretches along East 81st from 3rd to Lexington, also frequently features great Halloween facades. Indeed, in the past, Madonna’s neighbors at 158 East 81st Street and 150 East 81st Street have been known to transform their multimillion-dollar homes into full-fledged haunted houses. While Madonna generally does not dress up her own connected brownstones for Halloween, she does typically have a staff member hand out candy on Halloween Eve.

Gracie Mansion interior. Image courtesy of Hyperallergic

Close Encounters of the Mayor Kind at Gracie Mansion

Now an established NYC tradition, Gracie Mansion—home to Mayor de Blasio and his family—will once again be converted into a haunted house for Halloween. The front lawn of Gracie Mansion will also be transformed into a graveyard. As in the past, Mayor de Blasio and First Lady Chirlane McCray, who have also been known to don some very interesting costumes for the occasion, will be going all out. This year’s event promises spooky actors, props, face painting, music, and balloon makers and will run for three days—from October 25 to 27. The event is free, but participants need to pick up a ticket in advance. You can get a ticket online or by calling 311.

DING DONG THE WITCH IS DEAD (OR AT LEAST GONE)

For several years, the Upper East Side was home to the so-called “Witch of 77th Street” (sometimes also referred to as the “Wild Woman of 77th Street”). The neighborhood’s resident witch may have been linked to 77th Street in name but, in fact, her territory covered most of the neighborhood and parts of Yorkville. Before her arrest in 2017—reportedly for attacking a child—the “witch” was known for her piercing screams, which could be heard throughout the Lenox Hill, Carnegie Hill and Yorkville neighborhoods year-round, and for her habit of spitting on passer-bys (sometimes, even spitting directly into baby carriages). While most local residents considered the “Witch of 77th Street” an outsider, her arrest revealed that her choice of stomping ground wasn’t a coincidence. According to the New York Post, the “Witch of 77th Street” had close to $20,000 in cash on her at the time of her arrest.

While the West Village may take the top prize for Halloween parades and all-night parties, for a tamer and more family-friendly evening in a neighborhood with enough dentists and politicians to scare anyone, the Upper East Side has much to offer and don’t worry—you don’t have to live in the neighborhood to take home a bit of loot. Kids and parents from all five boroughs flock to the neighborhood on Halloween night.

Photo by Carter Horsley

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Contributing Writer Cait Etherington Cait Etherington has over twenty years of experience working as a journalist and communications consultant. Her articles and reviews have been published in newspapers and magazines across the United States and internationally. An experienced financial writer, Cait is committed to exposing the human side of stories about contemporary business, banking and workplace relations. She also enjoys writing about trends, lifestyles and real estate in New York City where she lives with her family in a cozy apartment on the twentieth floor of a Manhattan high rise.

Read Full Bio | Contact Cait Etherington

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78th Street—A Trick-or-Treating Hotspot

Haunted Houses

Close Encounters of the Mayor Kind at Gracie Mansion

DING DONG THE WITCH IS DEAD (OR AT LEAST GONE)

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